The Robertson's Sissy Ch. 03

**A quick note. The chapters of this story can fall into mutiple categories, group sex, reluctance/nonconsent and transgender/crossdresser. If any of these are not your taste than this story may not be for you.**

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Beep...Beep...Beep... Is all I heard as I woke the next morning. I smashed my alarm clock off and laid there completely hung over from all the booze I was fed the night before. I then recalled some of the events in my head which caused me to jolt out of bed.

"I can't believe I did that!" I thought in a panic.

I sat shocked as I came to the realization of what was happening. I thought back to sucking Chuck's cock and being forced to lick and swallow his massive load. Mentally I was disgusted but physically I felt my cock getting hard. No way this can be happening, I need to clear my head.

I woke and took a shower, had breakfast and finally sat on the couch watching some morning tv. I somehow fell back to sleep and was awoken to my phone going off. I didn't have to look to know who it was. I knew Lela was going to have me for the day. Normally I would have been excited but I was nervous as to what she had in store for me. I grabbed my phone and read her message.

"Hey sweetie, come by the house at Noon. Don't be late as we have an appointment we can't miss. Remember I own you for the day and you must do everything I ask in order to get your little video deleted. xoxo"

"Fuck me," I thought.

This fine ass woman had me by the balls. Normally that would be a good thing but not in this way. I thought of a way to get out of it, but it was no use. I had no choice but to see her though I was going to embrace the day. Anything she asked, I was going to do. I was going to attempt to have fun and enjoy whatever she planned and at the end I would get my video deleted.

"Just one day," I thought to myself.

I showered up and headed over to the Robertson's early so that I wasn't late for whatever Lela had planned.

I pulled up and saw the sexy cougar standing outside by her expensive silver Mercedes. As unhappy as I was, I couldn't help but feel weak for this woman. The mature latina looked good, wearing a white low cut shirt which made her breasts look like they were being strangled as the popped out the top. Black jean shorts which looked too short as the bottom of each ass cheek hung out the bottom. Dark sunglasses, white tennis shoes and her dark curly hair was down and across her back. God this woman kills me I thought as I got out of my car.

"There's my baby!" She said as she greeted me with the most passionate kiss. She threw me the keys and headed to the passenger side before saying, "Your driving stud!"

"Hey at least got to drive this sweet car," I thought to myself.

I hopped in, started it up and we were on our way. The drive started off quiet as she knew I wasn't the least bit happy. She tried warming up to me by placing her hand on my lap. She leaned over and kissed my cheek and my neck.

"I can tell you are mad. I get it and I'm sorry it went that way. I really like you and I want my plan to work out. I know how you guys think, anything other than fucking a hot chick your way is unacceptable. As you get older you learn to do what you enjoy and not what others expect you to enjoy. What happens behind closed doors, stays behind closed doors and that is how I want our relationship to be. I didn't want to blackmail you but I needed to make sure you tried everything I have planned. I really care for you and if you do everything I ask today I will delete your video and let you walk if you desire."

Her words were comforting, though I was still pissed off. She really knew how to get to me. She rested her head and on my shoulder and held my hand as I drove. We drove like this in silence, except for her giving directions and the sounds of her kisses. We finally pulled up to our destination, a small little shopping mall of independent stores.

"Here we are!" she announced in an excited manner as I parked in front of a store called 'Naughty Depot'.

It was a well known sex store in the area that we always joked about going to. God only knows what this woman had in store for me here. She kissed me one last time before hoping out of the car stating how she needed some new lingerie for later.

Maybe lingerie shopping for her wasn't going to be bad, especially if I got to enjoy it later. Inside she greeted Charles, the guy behind the counter. It was clear by their reaction and small talk that they knew each other well. We then moved through the endless racks of lingerie.

She was a woman on a mission and knew exactly what she wanted. She grabbed item after item throwing them in the basket. I took a minute to think about her in everything I saw and immediately started getting hard. I had to calm myself so I wasn't walking around with a tent in my pants.

I focused more on what she was doing. She was grabbing bras of assorted colors checking their sizes and throwing them in the cart. Panties, stockings, garter belts and everything else she saw fit. This woman dragged me around like a puppy but I would follow her anywhere in this store.

"Charles, I'm going to go in the back for a bit," she told him as she grabbed my hand and dragged me with her.

Here she started laying things out as she explained, "Normally the store doesn't allow people to try things but Charles lets me get away with it," She said with a big smile, "Sit back, relax and enjoy"

She turned and went into the bathroom as I took a seat on some boxes stacked against the wall. As I waited I felt my phone vibrate and saw a message from Jenna, "Hey Matt, I'm bored at home by myself and wanted to see if you are free to come over."

I knew she wanted me to fuck her but I was stuck with Lela for the day.

I quickly replied, "Hey Jenna, I would love to come see you but I'm away today visiting some relatives. Sorry babe."

Just as I finished the message I heard the bathroom door open. I looked up and saw Lela come out wearing a baby blue lingerie set. My jaw dropped as I stared. The bra was obviously too small causing her tits to explode out the top. I worked my way down her body noticing a garter belt, g-string and stockings all in matching baby blue.

"What do you think?" she asked.

I could do nothing but stare in amazement as she began walking over to me. I struggled to get my phone into my pocket before she jumped in.

"Leave your phone out, this will be better," she said as she slowly turned and sat on my lap.

She began grinding on me as she leaned back against me. She grabbed my hands and guided them up her body to her firm breasts, grabbing them and kneading them. Her breasts looked like they were screaming to be released, so I reached back to unhook her bra.

"No no no sweetie. We still have more to try," She laughed as she jumped off my lap and ran back to the bathroom.

My cock was as hard as a rock at this point and I couldn't wait for her to return. It felt like an eternity but the door opened again, this time she came out wearing a gold and black set. It looked silky smooth but barely covered her. Her breasts weren't being strangled this time but they were barely being held in.

As she came back to sit on me I noticed the g-string was now replaced by a pair of gold lace panties that left half of her ass cheeks exposed. Like before she began giving me a lap dance but was interrupted by my phone going off on the box next to me. She grabbed it before I could and stared at it before holding it up to my face.

"Is this the girl that wouldn't let you fuck her in the ass?" she asked.

I looked at the screen to see Jenna sent me a pic of her in bed, wearing only panties. The caption read, "I'm sorry you can't either."

Before I could answer Lela stated, "She a hot little slut! Too bad you won't be seeing her anymore. You're all mine now. A matter of fact, I don't want you talking to her anymore or at least until I'm done with you."

She gave me a very serious look before demanding, "I'm not fucking kidding, no more." I nodded in approval as she kissed me before returning to the bathroom.

She tried on a few more sets before asking which one I liked the most. Of course my reply was that I liked them all. She laughed and said she was getting them all but wanted to know which was my favorite. So I picked the first baby blue set that got me hard to begin with. With that she dragged me to the front and dropped everything on the counter.

"Hey Charles, I want to take all of these. I'll take them all as is but this blue one I want in the special sizes I gave you. Also do you have that special order I placed?"

"Absolutely", he answered as he bent down and came up with a small box before going to fetch the blue set for her.

I couldn't help but notice the weird smile and stare he gave me. I figured maybe because I wasn't her husband.

"Go get the car and I'll be right out," she said as she turned to me.

I went out and fetched the car before she shortly returned and loaded the trunk. She jumped in and instructed me to head to a certain area of town. As we left the parking lot she wasted no time.

"God I'm so horny, I wanna blow you so bad baby. That place always gets me wet," she said while undoing my shorts.

She wasted no time freeing my already hard cock and a few strokes later was bending over the center console taking me into her mouth. This wasn't a teasing blowjob with some foreplay and licking. Her goal was clear, she wanted my cum. Starting with small sucking motions of the head before sliding all the way down, taking all my length.

I felt amazing, driving around town in a sweet car and this amazing woman sucking my dick. She suddenly stopped, popping up where she undid her jean shorts pulling them down so I could play with her.

She was wearing a light green g-string which I found out matched her bra as she pulled her shirt up. She didn't remove it, just enough to show her bra covered breasts. She resumed her position and began sucking me again. Now this was a sight! Seeing her head bobbing up and down in my lap as she bent over the seat with her ass up in the air. With a free hand I began squeezing her breasts through her bra as she moaned on my cock.

As I played with her I had trouble keeping my eyes on the road. Her ass was so big and inviting as it seemed to swallow the g-string. I reached over and grabbed it before giving her a good smack. My smack caused her to yelp though muffled by my cock which was now down her throat. I reached under and began rubbing her pussy which was wetter than it was anytime before.

I stroked her clit as she moaned louder and louder. Knowing how horny she was I decided to give her a little more, sliding the g-string off to the side and exposing the sweet little asshole I plowed the night before. This time I would be gentle as I found her hole with my middle finger. I massaged it in small circles as her moans grew louder.

Occasionally I would press gently inside, just enough to get my finger tip in. At this point she was going to town on my cock and the vibrations of her moans set me over the edge. I gripped the wheel with both hands as I flooded her mouth with my load. As I expected my girl was a champ, softly stroking me while sucking the head of my cock clean. She milked me for every drop before sitting up and pulling her shirt down. I looked at her as she opened her mouth showing me the prize I gave her. It didn't take long before she swallowed it with a smile.

"Mmmmm baby you taste so good. Thank you."

I quickly joked, "You put a whole new meaning to good girls cleaning up their mess."

She laughed before adding, "God I love the taste of a man, I can't get enough of it."

She leaned in and kissed my cheek before whispering, "You'll learn to love it too. It's so rewarding."

Her statement made me realize that she had a lot more in store for me, putting my mind set back into the situation I was in. She snuggled up to me and directed me as we drove to the next destination. We finally pulled up to a small professional looking building which according to the sign seemed to be a bunch of doctors and other services.

She explained we were there so she could get some laser hair removal done. I love a perfectly hairless vagina so I had no complaints. We entered a small office on the first floor and I took a seat as Lela quietly talked to the woman at the counter.

"Wait her sweetie," Lela told me as she went back with the assistant.

As I waited I checked my phone to see that I missed another message from Jenna. It was another photo of her basically naked on her bed with the caption, "Tomorrow Night?"

"Fuck, how do I respond to this," I thought.

Let me make it sound like a yes but leave it open in case Lela locks me up again.

"I have a family dinner but I think tomorrow night can work." I responded.

Afterwards I remembered Lela's demand not to talk to her anymore. Before I was able to delete our convo the door opened. I rushed to put my phone away as Lela appeared around the corner. I got up, walking to the exit before she called out.

"Ummm where are you going?"

I answered, "Thought you were done and we were leaving."

"I am done, but now it's your turn" she said as she walked up to me.

She knew I was going to freak out so she got nice and close. As I opened my mouth she cut me right off.

"Remember I own you today, whatever I want or you know what. Now I want you perfectly smooth for me later," She leaned in and quietly whispered, "I want you to experience something new and plan on rimming the hell out of you when we get home."

"What the fuck?" I thought. I looked at her as she stared me down with a very serious look. I knew she meant business so I gave in and followed her to the back. The assistant lead me to a room, asking me to strip down and lay on the table while Lela took a seat in a chair.

It was cold and embarrassing to just lay there naked except for a towel. The assistant came back and asked how much we were doing.

Before I could speak Lela chimed in, "Everything from the neck down."

I just laid there helpless as the small zaps took all my body hair off, section by section. I suddenly heard my phone vibrate and watched Lela go to grab it.

I panicked, "Shit, if that's Jenna I'm fucked."

I watched her face for her response but her expression never changed.

She told me, "It's nothing, just an email."

She put the phone back down as I breathed a sigh of relief.

"I just need to get through tonight," I thought, "just through tonight."

It seemed like an eternity but I was finally done getting all the hair zapped off my body. My cock looked weird as I have never seen it so hairless and my clothes felt a bit different. Other than that it wasn't too bad.

We left the office and drove back to the Robertson's, the whole ride Lela held my hand, resting her head on my shoulder. It was times like this I enjoyed being with her, though I knew I had to tip toe my actions until that video was gone.

I carried in all the stuff we purchased and dropped it off on her bed as she requested. She asked me to join her in the living room where she was making us a few drinks. I sat on the couch as she joined me, handing me a big glass of scotch.

She sat next to me sipping her usual wine before slipping her hand on to my lap. I could tell from the look in her eyes and her big smile that she was almost ready for some action. We sat there leaning on each other as we drank and had small talk.

It was clear she was getting me drunk again as she kept filling up my glass and encouraging me to finish. I knew this is what got me in trouble the night before but I couldn't turn her down. I had to do everything she asked. It wasn't long before the booze started getting me sloppy.

"Let's take a shower sweetheart," she said as she lead me to the master bathroom. I jumped at the opportunity to join this sexy cougar in the shower. This was the best thing, I could stop drinking and maybe sober up there. In the shower we made out as we washed each other while exploring each others body. Her hand made her way to my now hairless cock as she stroked it.

"God I love you so much more without any hair. I know it must be weird for you but you will get used to it. Plus it makes it look way bigger, not that I'm complaining," she said with a laugh.

We ended our shower and dried ourselves off. She asked me not to get dressed and to join her in the bedroom, so in my drunken haze I followed. She lead me to the bed where she laid out some of the new lingerie.

"Which one should I wear for you tonight?" she asked in an exciting manner.

"The alcohol was affecting my memory and I could only remember the first baby blue set, so I told her to wear that.

"mmmmm I got other plans for that one, I think I'll go with the black and red one," she suggested as she pulled out all the pieces to that set as well as the blue one.

"What is your plan for wearing the blue one?" I asked waching her laying it out.

She got really close to me, kissed me and said, "Baby, that's not for me to wear. That's for you."

I suddenly realized her request at the store for the "special size and her special order."

I almost freaked out but even in my drunken state I knew I had to submit to any request she gave. I reluctantly nodded and she smiled knowing I was learning to obey her. We got dressed together as she walked me through wearing each piece. The g-string was first, luckily she had Charles replace the woman's one with a male version which had a pouch for my now hairless cock.

Garter belt was next followed by the stockings. I'm not going to lie, the feel of the fabrics again my skin was amazing. Lela helped me clip the straps of the garter belt as I felt something I didn't expect. The feel of the sexy lingerie against my now smooth skin caused my cock to grow. Was I really enjoying this?

Last was the bra which she helped me hook on. I stared awkwardly as the cups were way too big, but of course Lela had a plan. She reached into the box and pulled out two fake silicone breast inserts.

"I like my bitches big," she laughed as she inserted them into the cups. She lead me as she carried her special box to the walk in closet.

There I watched her put on a very tight yet short blue dinner dress. The dress showed all her curves leaving little to the imagination. God this woman's body is amazing I thought as my cock screamed to be freed. My gaze was soon interrupted as she threw something at me. I caught it and held it out. It was the same dress she was wearing but in black.

"That's your's my love, put it on," she ordered in a calm voice.

I sat there trying to squeeze into the dress as Lela began sifting through her box. I finally got it on, it was tight but felt good against my skin. I looked at her for approval and she smiled as she approached me. She gave me a kiss before bringing her hands up showing me a curly brunette wig that almost matched her own.

I didn't protest as she fit it on me, moving it around in an attempt to make it look right. Finally she turned me around so I could see myself in the mirror.

"What the fuck?" I thought.

Maybe it was the booze but at first glimpse I could have fooled myself. As I stared it became clear why Lela picked me. Other than the fact she knew I was smitten by her, I had a small frame for a guy, I guess I looked rather womanly.

"Go take a seat in the bathroom, I'll be right back," Lela excitedly requested.

I did as instructed and she quickly joined me holding two more drinks.

"Fuck me," I thought.

Last thing I needed was more booze in my system but if she said drink I had to obey. We sat there drinking as she started messing around with some make up. It felt really weird but in my drunken state I couldn't help but stare at how beautiful she was. Not only that but she wouldn't stop smiling, it was clear she was loving this and deep down I enjoyed making her happy.